3-(4-甲酰基三唑-1-基)苯甲腈 | 916150-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(4-甲酰基三唑-1-基)苯甲腈
• 英文名称: 3-(4-formyl-1H-1,2,3-triazol-1-yl)benzonitrile
• 英文别名: 4-carboxaldehyde-1-(3-cyanophenyl)-1H-1,2,3-triazole；3-(4-formyltriazol-1-yl)benzonitrile
• CAS: 916150-99-7
• 化学式: C₁₀H₆N₄O
• 分子量: 198.184
• InChiKey: ZYOKUHZAIVLERG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-甲酰基三唑-1-基)苯甲腈 在 二甲氨基三氟化硫 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 5-(3-(4-(difluoromethyl)-1H-1,2,3-triazole-1-yl)phenyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Novel 1,2,3-Triazole Derivatives for Use against Mycobacterium tuberculosis H37Rv (ATCC 27294) Strain

  摘要：

  The purpose of this study was to prepare various 4-substituted N-phenyl-1,2,3-triazole derivatives using click chemistry. The derivatives were screened in vitro for antimicrobial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294) using the Alamar Blue susceptibility test. The activity was expressed as the minimum inhibitory concentration (MIC) in mu g/mL (mu M). Derivatives of isoniazid (INH), (E)-N'-[(1-aryl)-1H-1,2,3-triazole-4-yl)methylene] isonicotinoyl hydrazides, exhibited significant activity with MIC values ranging from 2.5 to 0.62 mu g/mL. In addition, they displayed low cytotoxicity against liver cells (hepatoma HepG2) and kidney cells (BGM), thereby providing a high therapeutic index. The results demonstrated the potential and importance of developing new INH derivatives to treat mycobacterial infections.

  DOI：

  10.1021/jm2003624
• 作为产物：
  描述：

  3-叠氮苯甲腈 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 戴斯-马丁氧化剂 、 sodium ascorbate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 12.5h， 生成 3-(4-甲酰基三唑-1-基)苯甲腈
  参考文献：
  名称：

  通过 7-脱氮腺苷和接头修饰增强烟酰胺 N-甲基转移酶双底物抑制剂活性

  摘要：

   [显示省略]

  DOI：

  10.1016/j.bioorg.2023.106963

文献信息

• Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives
  作者：Marilia S. Costa、Núbia Boechat、Érica A. Rangel、Fernando de C. da Silva、Alessandra M.T. de Souza、Carlos R. Rodrigues、Helena C. Castro、Ivan N. Junior、Maria Cristina S. Lourenço、Solange M.S.V. Wardell、Vitor F. Ferreira

  DOI：10.1016/j.bmc.2006.08.019

  日期：2006.12

  The aim of this work was to describe the synthesis, the in vitro anti-Mycobacterium tuberculosis profile, and the structure-activity relationship (SAR) study of new N-substituted-phenyl-1,2,3-triazole-4-carbaldehydes (3a-l). The reactions of aromatic amine hydrochlorides with diazomalonaldehyde (1) produced several N-substituted-phenyl-1,2,3-triazole-4-carbaldehydes (3a-l) in moderate-to-good yields

  这项工作的目的是描述新型N-取代的苯基-1,2,3-三唑-4-甲醛的合成，体外抗结核分枝杆菌谱以及结构-活性关系（SAR）研究（ 3a-1）。芳族胺盐酸盐与重氮丙二醛（1）的反应以中等至良好的产率产生了几种N-取代的苯基-1,2,3-三唑-4-甲醛（3a-1）。为了研究二氟亚甲基对这些化合物的抗分枝杆菌活性的影响，用DAST氟化三唑可将相应的甲醛化合物以优异的产率转化为新的二氟甲基衍生物（4a-1）。所有化合物的表征均通过分光光度法进行，另外1-（4-甲基苯基）-1,2,3-三唑-4-甲醛通过X射线晶体学测定。已经针对化合物对结核分枝杆菌H37Rv菌株（ATCC 27294）的抑制活性筛选了化合物（3a-1）和（4a-1），并且它们全部都能够抑制细菌的生长。有趣的是，与目前用于治疗结核病的药物相似，3a和3k的MIC值为2.5mug / mL表现出最好的抑制作用。我们的SAR研究表明，氢键
• Novel 1,2,3-Triazole Derivatives for Use against <i>Mycobacterium tuberculosis</i> H37Rv (ATCC 27294) Strain
  作者：Nubia Boechat、Vitor F. Ferreira、Sabrina B. Ferreira、Maria de Lourdes G. Ferreira、Fernando de C. da Silva、Monica M. Bastos、Marilia dos S. Costa、Maria Cristina S. Lourenço、Angelo C. Pinto、Antoniana U. Krettli、Anna Caroline Aguiar、Brunno M. Teixeira、Nathalia V. da Silva、Priscila R. C. Martins、Flavio Augusto F. M. Bezerra、Ane Louise S. Camilo、Gerson P. da Silva、Carolina C. P. Costa

  DOI：10.1021/jm2003624

  日期：2011.9.8

  The purpose of this study was to prepare various 4-substituted N-phenyl-1,2,3-triazole derivatives using click chemistry. The derivatives were screened in vitro for antimicrobial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294) using the Alamar Blue susceptibility test. The activity was expressed as the minimum inhibitory concentration (MIC) in mu g/mL (mu M). Derivatives of isoniazid (INH), (E)-N'-[(1-aryl)-1H-1,2,3-triazole-4-yl)methylene] isonicotinoyl hydrazides, exhibited significant activity with MIC values ranging from 2.5 to 0.62 mu g/mL. In addition, they displayed low cytotoxicity against liver cells (hepatoma HepG2) and kidney cells (BGM), thereby providing a high therapeutic index. The results demonstrated the potential and importance of developing new INH derivatives to treat mycobacterial infections.
• Enhancing nicotinamide N-methyltransferase bisubstrate inhibitor activity through 7-deazaadenosine and linker modifications
  作者：Pengyu Li、Cuicui Xia、Xiangqian Kong、Jiancun Zhang

  DOI：10.1016/j.bioorg.2023.106963

  日期：2024.2

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